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ChemicalBook CAS DataBase List 5-(4-FLUOROPHENYL)-2-METHYL-3-FUROIC ACID
111787-88-3

5-(4-FLUOROPHENYL)-2-METHYL-3-FUROIC ACID synthesis

4synthesis methods
-

Yield:111787-88-3 93%

Reaction Conditions:

Stage #1: methyl 5-(4-fluorophenyl)-2-methylfuran-3-carboxylatewith methanol;sodium hydroxide;water at 20;
Stage #2: with hydrogenchloride in water;

Steps:

95.2

Methyl 5-(4-fluorophenyl)-2-methyl-3-furancarboxylate (15.36 g, 65.58 mmol) and sodium hydroxide (5.25 g, 131 mmol) were stirred in methanol (100 ml) and water (50 ml) at room temperature overnight. The reaction solution was concentrated, diluted with water, acidified with conc. hydrochloric acid and washed three times with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to give the objective substance. pale-yellow crystal yield 13.42 g, 93% mp 217-218°C; 1H-NMR (CDCl3-DMSO-d6, 200MHz) δ 2.65 (3H, s) , 6.83 (1H, s) , 7.07 (2H, t, J = 8.6 Hz), 7.60 (2H, dd, J = 5.0 Hz, 8.8 Hz); IR (KBr) 3100-2500, 1694, 1505, 1474, 1233, 774 cm-1; Anal. Calcd for C12H9FO3 : C, 65.46; H, 4.12. Found: C, 65.50; H, 4.15.

References:

EP1362846,2003,A1 Location in patent:Page/Page column 79